Events happening in Oakville.

Saturday, August 22nd

10:00AM – 4:00PM

Youth Home Run Derby

Lead Off Youth Home Run Derby invites young hitters to step up to the plate and compete in a single-elimination home run competition. Two divisions accommodate different age groups and skill levels: a 200-foot fence for 12U–14U and power-hitting 11U players, and a 125-foot fence for 8U–10U players. All players are welcome, whether from house league or rep teams. Competition format: Round 1 features 10 swings per player, with a minimum of 15 advancing after hitting at least one home run. Round 2 narrows the field to the top 10 with another 10 swings. The Championship Round crowns the winner through a 10-out format, with a 5-swing tie-breaker if needed. Awards include a custom championship ring for first place, silver and bronze medals for second and third place, and finalist medals for 7th–10th place finishers. Registration begins at 9:00 AM, with first pitch at 10:00 AM. Early bird pricing is available until July 2, after which rates increase. Spots are limited.

Palermo Way, Oakville, ON L6M, Canada

Saturday, August 22nd

12:00PM – 8:00PM

Pre Festival Vendors Exhibition

The Pre Festival Vendors Exhibition, hosted by HCCA, showcases handcrafted products and artworks from talented vendors. Attendees will find a diverse range of unique items, including handmade jewelry, paintings, and other creative work. August 22, 2026, at 12:00 PM 1280 Dundas Street West, Oakville

St. Volodymyr Event Centre - SV Event Centre · Free

Sunday, August 23rd

10:00AM – 12:00PM

Bloom & Build Network & Vendor Fair

A networking and vendor fair where attendees can meet local business owners and vendors, discover products, and make professional connections in a relaxed setting.

Touchdown Coworking Space · Free

Sunday, August 23rd

5:00PM – 9:00PM

West End Jazz Presents: A Tribute to Peggy Lee

The West End Jazz series presents a dinner theatre production. Attendees may choose to enjoy dinner, attend the show only, or both. Doors open at 4:00 PM, dinner is served at 5:00 PM, and the show begins at 6:00 PM. Peggy Lee was an iconic jazz singer and actress, celebrated for her signature sultry vocal style. Her best-known hits include "Fever," "Mañana," and "Is That All There Is?" Shannon Butcher delivers Peggy Lee's songs with remarkable authenticity — closing your eyes, you may feel as though Peggy Lee herself is on stage.

Oakville Conference Centre

Wednesday, August 26th

4:00PM – 7:00PM

Where the Light Lands: Impressions of Muskoka by Rick Worthington

Opening reception for Where the Light Lands: Impressions of Muskoka, featuring work by contemporary impressionist Rick Worthington.

· Free

Thursday, August 27th

10:00AM

Bronte Book Club

This month's book club will discuss "What Have You Done?" by Shari Lapena. Copies are available to borrow at the Woodside Branch on a first-come, first-served basis; quantities are limited. The book club session takes place at Taste of Colombia Café, 67 Bronte Road. Free parking is available behind the café; paid street parking is also an option. Those parked behind the café may use the back entrance. Registration is required. Attendees will develop critical thinking, creativity, collaboration, communication, information literacy, media literacy, technology literacy, flexibility, leadership, initiative, productivity, and social skills. To cancel a registration, log into MyEvents using your library card (or use the reference number from your confirmation email), call your local branch, or email oplreference@oakville.ca. Have the program title, program date, and registered names ready. For program guidelines and frequently asked questions, review the Program FAQ.

Community Location

Thursday, August 27th

6:00PM

WORK IT GIRL KIDS FREE WORKSHOPS - OAKVILLE/MISSISSAUGA LOCATION

Work It Girl Workshop Series — Oakville/Mississauga Edition offers free monthly confidence-building leadership and dance workshops for girls aged 6–11. The program combines upbeat dance routines with mindset skills taught through storytelling, covering positive self-talk, honouring uniqueness, and personal leadership. During each workshop, participants learn choreography while building team-building and self-expression skills in a supportive, welcoming environment. The workshops are free and open to all girls who love dance, music, and self-expression. For questions or more information, email info@janetco.live or follow @workitgirlmovement on Instagram.

The Tumbling Gym · Free

Friday, August 28th

6:30PM

Bronte's Dominican Bachata Party 2026

Bachata Nights 💃 at Bronte Market Square A free, 13-week summer celebration for all ages featuring live music and dancing. Tiana Adames leads the event, bringing rhythm and community spirit to the heart of Bronte. Every Friday, June 19 – September 11, 6:30 PM – 9:30 PM at Bronte Market Square.

Bronte Market Square – 2445 Lakeshore Rd W

Saturday, August 29th

10:00AM – 2:00PM

Put your Paws up

Meet the groomer and trainer. Get a professional photo with your best friend, and enjoy treats from Tailblazers.

Saturday, August 29th

3:00PM – 10:00PM

CRAFT Live-Afro Caribbean Canadian Waterfront Fete

This celebration honours the vast contributions and influences of African, Caribbean, and Black Canadians in shaping the community, culture, and economy. The event features live music spanning Soca, Calypso, Reggae, Steelpan, R&B, Afro Beats, Disco, Jazz, Blues, and Funk & Soul, plus a live DJ and vendors. Free and open to all ages.

Bronte Heritage Waterfront Park

Sunday, August 30th

7:00PM – 8:30PM

Deep Healing & Restorative Yoga + Sound Bath

Deep Healing & Restorative Yoga + Sound Bath 🤍 An intimate evening for women to connect to their mind, body, and spirit in a safe space. This is a nourishing night of yoga, sound, reflection, and connection — a space to slow down, soften, and begin again. If you've been holding on to something you're ready to let go of, this space is for you. The evening includes a 60-minute grounding yoga practice, a deeply restorative sound bath, a guided journal practice, nourishing tea, and space for community, presence, and genuine connection. Attendees will have an opportunity to release spiritual, physical, and emotional pain. Come as you are. Leave a little lighter. For questions, contact Lexi at lexi@soul-work.ca or 905-616-8266.

Upasna - A Hot Yoga Studio · Free

Thursday, September 3rd

Paint Nite • Dave & Busters Oakville • Oakville

Paint Night 🎨 Teens and up are invited to paint Dawn of New Beginnings together in a beginner-friendly setting. All supplies are included. Held at Dave & Busters Oakville.

Dave & Busters Oakville

Saturday, September 5th

11:00AM – 5:00PM

Card Yard

Card Yard is hosting a collectibles convention bringing together vendors, collectors, and hobby enthusiasts in one welcoming space. The event focuses on trading card games, sports cards, and comics. Attendees can browse, buy, sell, and trade cards and comics while connecting directly with vendors and fellow collectors. Entry is free. The event is designed to support the local collectibles community.

OE Banquet & Conference Centre · Free

Sunday, September 6th

Sound Bath & Energy Activation | Oakville

Deep relaxation and stress relief through Kundalini Activation & Sound Bath, guided by two certified facilitators.

INYE YOGA

Tuesday, September 8th

7:30PM

Tartan Terrors: 30 Years of Terror

The Tartan Terrors are celebrating 30 years of high-energy Celtic music. Their award-winning sound blends traditional Celtic music with rock and roll, featuring bagpipes, drums, fiddles, guitars, and dancing. The group has released 11 CDs and numerous DVDs, and performed thousands of live shows across more than 48 U.S. states and 5 countries. They have played at iconic venues including the Iridium on Broadway, the Dublin Irish Festival, and Loon Mountain in New Hampshire, and appeared on Good Morning America. The Tartan Terrors have also performed for Queen Elizabeth and at President Clinton's inauguration. Over the years, they have shared the stage with Eileen Ivers, Dropkick Murphys, and Ally the Piper, among others. As Hunters Bay Radio noted, "These guys are high-energy and they leave everything on stage."

Oakville Centre — AEG Liebherr Auditorium

Wednesday, September 9th

10:00AM – 11:30AM

Halton Memory Cafe – Oakville

The Halton Memory Café is a welcoming social gathering for people living with dementia and their care partners to attend together. Each session offers a relaxed opportunity to connect with others, enjoy meaningful conversation, participate in light activities, and spend time in a supportive community setting. The Memory Café is not a clinical program or formal education session. It is designed to be friendly, inclusive, and comfortable for both the person living with dementia and their care partner. Registration is free. Advance registration is requested so organizers can plan appropriately for seating, refreshments, and activities. Space may be limited.

Glen Abbey United Church · Free

Thursday, September 10th

6:00PM

Adult Book Club

This month's discussion focuses on The Bandit Queens by Parini Shroff. Copies are available on a first-come, first-served basis at Sixteen Mile branch; quantities are limited. Attendees are invited to drop in — no registration required. The group explores a wide range of titles, genres, and authors, with discussions focused on the books themselves. The Oakville Public Library welcomes people of all backgrounds and abilities. All participants are asked to follow the Customer Code of Conduct and review the Programming FAQ for additional guidelines.

Sixteen Mile Branch

Friday, September 11th

3:45PM – 11:00PM

10TH ANNUAL KERRFEST

Kerrfest 🎉 celebrates its 10th anniversary with a two-day street party and outdoor music festival featuring Canadian artists, local food vendors, an artisan market, and family-friendly activities. The event runs September 11–13, 2026, at Westwood Park in Oakville, Ontario, and is presented by the Kerr Village BIA.

Westwood Park · $11.98 – $267.58 CAD